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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 77 Cottages in Chester with updated reviews, rates, and availability.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (107)
"Spectacular view and very convenient to USMA. "
The price is SAR 630
SAR 919 total
includes taxes & fees
24 Feb - 25 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Mountain House Escape - 1 Hour from NYC
Exterior

Mountain House Escape - 1 Hour from NYC

10.0 out of 10, Exceptional, (7)
"We recently had the pleasure of staying at Deer Hill in Warwick, NY, and it truly exceeded our expectations. The property is set on three-acre expanse in a lovely, and ultra-quiet neighborhood. It was an ideal home for our annual family gathering, which includes our 3 adult children, spouses and two young grandchildren. The large in-ground pool was a hit, and was a source of fun and relaxation throughout our stay. The pool has a shallow end and an 8-foot deep end. The spacious great room served...
Mountain House Escape - 1 Hour from NYC
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Dining

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

2.0 star property
8.0 out of 10, Very Good, (2)
"Nice"
The price is SAR 938
SAR 1,926 total
includes taxes & fees
24 Feb - 25 Feb
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
The Cottage at Millpond Falls is a romantic getaway -- an luxury experience you won't forget.

Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick

10.0 out of 10, Exceptional, (142)
"Such a beautiful location. The cottage is quant while having all the modern updates. The hosts have carefully left an array of coffee and welcome goodies, including fresh eggs from their ducks. Will be back! "
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Home Sweet Home ...

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (98)
"Great Highland Lakes Cottage! Clean & well stocked kitchen. Be careful going up or down Breakneck Rd. Thus time of year every view is beautiful! We did lots of small road trips taking in the sites and autumnal views!!"
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Cozy Cottage Getaway, Grill, Walk to Lake
Enjoy the morning sunlight streaming through the windows while staying cozy inside. Pull down filter shades on all windows for privacy. (Use of fireplace is not allowed unfortunately!)

Cozy Cottage Getaway, Grill, Walk to Lake

9.8 out of 10, Exceptional, (17)
"The cottage was perfect for our weekend trip to visit our son at West Point. A picturesque drive to West Point, the cottage was so cute and was full of thoughtful amenities. Had we had the time to cook, the kitchen was stocked with spices, condiments, and cooking oils to make it easy to do so. The complimentary coffee was perfect as we arrived late and the stores were closed. The host was easy to contact and so kind and thoughtful. We will definitely book again. "
The price is SAR 615
SAR 1,475 total
includes taxes & fees
25 Feb - 26 Feb
Cozy Cottage Getaway, Grill, Walk to Lake
Historic 1800's Cornwall-On-Hudson Cottage!
Cornwall-On-Hudson Vacation Rental | 2BR | 2BA | Stairs Required | 2,000 Sq Ft

Historic 1800's Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (22)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic 1800's Cornwall-On-Hudson Cottage!
Putnam Valley Vacation Rental: Patio & Lake Views!
Putnam Valley Vacation Rental | 3BR | 2BA | 7 Steps Required to Enter

Putnam Valley Vacation Rental: Patio & Lake Views!

9.8 out of 10, Exceptional, (12)
"Cozy, clean property. We had everything we needed for a 3-night stay for West Point Family Weekend. Several stores & restaurants conveniently nearby. Host Neury was most accommodating. Incredible views & scenery!!"
Putnam Valley Vacation Rental: Patio & Lake Views!
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Private kitchen

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

9.8 out of 10, Exceptional, (9)
"We had a great stay in this cozy cabin! The beds were comfortable and the views of the farm and deer were beautiful ! Communication with Ginny was quick and she let us adjust our dates of stay when needed. 😊"
The price is SAR 619
SAR 1,164 total
includes taxes & fees
24 Feb - 25 Feb
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Putnam Valley Vacation Rental: Patio & Lake Views!
Terrace/patio

Putnam Valley Vacation Rental: Patio & Lake Views!

3.0 star property
Putnam Valley Vacation Rental: Patio & Lake Views!
A romantic cottage and artist's retreat looking down over an enchanted lake
Stunning views

A romantic cottage and artist's retreat looking down over an enchanted lake

9.4 out of 10, Exceptional, (96)
"It was an awesome stay we loved the couple days we got to spend there!!"
A romantic cottage and artist's retreat looking down over an enchanted lake
Beautiful Cottage in Hudson Valley w/Pool & Views
Interior

Beautiful Cottage in Hudson Valley w/Pool & Views

10.0 out of 10, Exceptional, (11)
"The house was beautifully decorated and furnished well. We enjoyed the large kitchen. The host responded to questions quickly and well. It is a beautiful region. Views were lovely, and roads and driveway were scraped of snow before we had time to think about it. "
Beautiful Cottage in Hudson Valley w/Pool & Views
Hello Small Stone
Exterior

Hello Small Stone

9.6 out of 10, Exceptional, (4)
"The house has a lot of character and the outdoor areas are really peaceful. The owner just needs to resolve the issue with sulfur in the water because the rotten egg smell is too strong to tolerate."
The price is SAR 675
SAR 1,136 total
includes taxes & fees
26 Feb - 27 Feb
Hello Small Stone
NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!
Living area

NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!

10.0 out of 10, Exceptional, (5)
"The house is even more beautiful than the photos. From the spa-like bathrooms, to toys and books for kids, to the little extra amenities like qtips and bandaids, it was the perfect getaway for everyone in our party of all ages."
NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!
Dreamy Hudson Valley Cottage w/ State Park Views
Garrison Vacation Rental | 1BR | 1BA | 650 Sq Ft | Steps Required

Dreamy Hudson Valley Cottage w/ State Park Views

9.8 out of 10, Exceptional, (12)
"We loved our two nights at this perfect, comfortable cottage in the Garrison woods. Communication with Ashley was terrific, very prompt and welcoming. The house was very clean and we had a great view. Thank you for a great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views
Lakefront Getaway : Mountain & Lakes views
Property grounds

Lakefront Getaway : Mountain & Lakes views

10.0 out of 10, Exceptional, (4)
"The property is beautiful and relaxing, exactly what we needed. The house is cozy with full amenities needed if you were staying longer than just a few nights."
Lakefront Getaway : Mountain & Lakes views
Cozy Haven: A Romantic Retreat in our Tiny House!
Room

Cozy Haven: A Romantic Retreat in our Tiny House!

7.0 out of 10, Good, (9)
"we enjoyed the cozy home it is a nice place to get away"
The price is SAR 563
SAR 990 total
includes taxes & fees
9 Mar - 10 Mar
Cozy Haven: A Romantic Retreat in our Tiny House!
Port Jervis Home ~ 8 Acres w/ Mountain View!
Property grounds

Port Jervis Home ~ 8 Acres w/ Mountain View!

3.0 star property
Port Jervis Home ~ 8 Acres w/ Mountain View!
Delightful Home w/ Fire Pit, Walk to Lake!
Living area

Delightful Home w/ Fire Pit, Walk to Lake!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very clean, easy access perfect location near my family for a birthday, silvia was very quick to respond to any questions!!"
Delightful Home w/ Fire Pit, Walk to Lake!
Relaxing New York Home w/ Boat Dock & Lake View!
Living area

Relaxing New York Home w/ Boat Dock & Lake View!

2.5 star property
Relaxing New York Home w/ Boat Dock & Lake View!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chester

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!
Exterior

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (107)
"Spectacular view and very convenient to USMA. "
The price is SAR 630
SAR 919 total
includes taxes & fees
24 Feb - 25 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
Vernon Living Room

Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

9.0 out of 10, Wonderful, (76)
"We enjoyed our stay at this condo. There was plenty of space for us to hang out and sleep. We used the kitchen a lot and for the most part it was well equipped. We could have used more things like larger bowls to mix things or for chips. The downstairs bathroom shower could also use a curtain so that the water doesn’t get everywhere. The condo was easy to find and check in. The owner reached out to make sure we were good which was nice. Overall our family was happy with the unit "
The price is SAR 656
SAR 1,666 total
includes taxes & fees
3 Mar - 4 Mar
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do cottages in Chester cost?
Cottages in Chester range between SAR 563 and SAR 938 per night. These stays offer a chance to get in touch with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Chester with Expedia?
Reserving a cottage in Chester is as easy as clicking on your travel dates and choosing an ideal place for a vacation in nature. From ritzy retreats to low-cost properties and cottages that have amenities like laundry facilities, Expedia has something for all traveler tastes. As for awesome deals? We’ve got you covered!
How can I find cheap cottages in Chester?
The easiest way to compare cheap cottages in Chester is with Expedia’s filter tool. Fine-tune your search results by amenities, star rating and budget to take advantage of awesome bargains with only a few clicks.